tioguanine
CHEBI:9555 EXACT SEEDED antiviralcytotoxicenzyme inhibitor
A 2-aminopurine that is the 6-thiono derivative of 2-amino-1,9-dihydro-6H-purine. Incorporates into DNA and inhibits synthesis. Used in the treatment of leukaemia.
Structure
| Standard InChIKey | WYWHKKSPHMUBEB-UHFFFAOYSA-N |
|---|---|
| SMILES | C1=NC2=C(N1)C(=S)N=C(N2)N |
| Stereochemistry | fully defined |
| Cross-references | pubchem:2723601 |
Filing pathway
Alkaloids — computed by NPClassifier npclassifier.gnps2.org@2026-09-07, which is why it is pinned rather than recomputed. The gene cluster's asserted class is other, from MIBiG.
Producer organisms 1
A claim that this taxon makes the compound. The basis says what the evidence addressed — a knockout and a database assertion are not the same claim.
| Taxon | Basis | Cluster | Evidence |
|---|---|---|---|
| Erwinia amylovora CFBP1430 NCBITaxon:665029 |
SOURCE_ASSERTION | mibig:BGC0001992 | PMID:29947149 |
Occurrences 2
Somebody found the compound in this organism and cited it. That is not a claim that the organism makes it, and nothing here promotes one to the other.
| Taxon | Source | Reference |
|---|---|---|
| Paris polyphylla var. chinensis NCBITaxon:221254 |
LOTUS | DOI:10.1016/J.JPBA.2011.12.027 |
| Pseudomonas NCBITaxon:286 |
LOTUS | DOI:10.7164/ANTIBIOTICS.24.328 |
Biosynthetic gene clusters 1
| Accession | Host | Locus evidence | Genome |
|---|---|---|---|
| mibig:BGC0001992 | Erwinia amylovora CFBP1430 NCBITaxon:665029 |
CLUSTER_UNSTATED | genbank:NC_013971.1 |
A locus claim and a taxon claim are different questions. Heterologous expression settles the first and leaves the second where the isolation report left it.
Bioactivities 25
| Assay | Result | Reference |
|---|---|---|
| A CellTox Green Cytotoxicity Assay to monitor cytotoxicity in HEK293 cells - 16 hour | 15.089 uM | pubchem.aid:1224888 |
| A High-Content qHTS Against Drug Library for the Identification of Small Molecules that Inhibit DYT1 Early Onset Primary Dystonia-Associated Cell Pathology | 15.8489 uM | pubchem.aid:1645839 |
| A High-Content qHTS Against Drug Library for the Identification of Small Molecules that Inhibit DYT1 Early Onset Primary Dystonia-Associated Cell Pathology | 15.8489 uM | pubchem.aid:1645839 |
| A cytotoxicity screen of small molecule inhibitors of the PhoP regulon in Salmonella typhi identified in the primary screen | EC50 0.32 uM | pubchem.aid:2252 |
| A quantitative high throughput screen for small molecules that induce DNA re-replication in MCF 10a normal breast cells. | 1.2995 uM | pubchem.aid:624296 |
| A screen for inhibitors of the PhoP regulon in Salmonella Typhi using a modified counterscreen | IC50 6.297 uM | pubchem.aid:1985 |
| Acetylcholinesterase (AChE) small molecule antagonists: colormetric cell-based qHTS assay | 21.8794 uM | pubchem.aid:1347395 |
| BET inhibitor-based combinations targeting novel dependencies in MECOM-rearranged (r) AML: AML-191 cell line | 0.8327 uM | pubchem.aid:2202236 |
| BET inhibitor-based combinations targeting novel dependencies in MECOM-rearranged (r) AML: AML-194 cell line | 3.7197 uM | pubchem.aid:2202237 |
| BET inhibitor-based combinations targeting novel dependencies in MECOM-rearranged (r) AML: HNT-34 cell line | 3.3152 uM | pubchem.aid:2202234 |
| BET inhibitor-based combinations targeting novel dependencies in MECOM-rearranged (r) AML: MV-4-11 cell line | 0.2955 uM | pubchem.aid:2202233 |
| BET inhibitor-based combinations targeting novel dependencies in MECOM-rearranged (r) AML: OCI-AML3 cell line | 0.4174 uM | pubchem.aid:2202232 |
| BET inhibitor-based combinations targeting novel dependencies in MECOM-rearranged (r) AML: SET-2 cell line | 0.7422 uM | pubchem.aid:2202231 |
| BET inhibitor-based combinations targeting novel dependencies in MECOM-rearranged (r) AML: UCSD-AML1 cell line | 2.9547 uM | pubchem.aid:2202235 |
| Biochemical firefly luciferase enzyme assay for NPC | 40.5334 uM | pubchem.aid:624030 |
| Caspase-3/7 induction in CHO-K1 cells by small molecules, qHTS cell viability counter screen | 5.31 uM | pubchem.aid:1346979 |
| Caspase-3/7 induction in CHO-K1 cells by small molecules, qHTS cell viability counter screen | 9.6885 uM | pubchem.aid:1346979 |
| Caspase-3/7 induction in CHO-K1 cells by small molecules, qHTS cell viability counter screen | 3.7578 uM | pubchem.aid:1346979 |
| Caspase-3/7 induction in HepG2 cells by small molecules, qHTS cell viability counter screen | 5.958 uM | pubchem.aid:1346981 |
| Caspase-3/7 induction in HepG2 cells by small molecules, qHTS cell viability counter screen | 8.6349 uM | pubchem.aid:1346981 |
| Caspase-3/7 induction in HepG2 cells by small molecules, qHTS cell viability counter screen | 13.3332 uM | pubchem.aid:1346981 |
| Cellular viability qHTS for adrenocortical cancer (ACC) cell line NCI-H295R | 0.7308 uM | pubchem.aid:1963990 |
| Cellular viability qHTS for adrenocortical cancer (ACC) cell line NCI-H295R | 1.122 uM | pubchem.aid:1963990 |
| Cellular viability qHTS for adrenocortical cancer (ACC) cell line SW-13 | 3.2643 uM | pubchem.aid:1963989 |
| Cellular viability qHTS for adrenocortical cancer (ACC) cell line SW-13 | 2.8184 uM | pubchem.aid:1963989 |
Elsewhere in the fleet
- AntibioticMech — CHEBI:9555 (same structure, same inchikey)
Open questions 1
name-disagreement — ChEBI calls this structure 'tioguanine' and MIBiG calls it 'thioguanine'. They share a Standard InChIKey, so if the names denote different compounds then one upstream record has the wrong structure. Check which.
Provenance
| Source concept | Source | Version |
|---|---|---|
| BGC0001992 | MIBIG | 3 |
| CHEBI:9555 | CHEBI | 3-star |
This page is generated from data/natural_products/alkaloids/tioguanine.yaml, which is generated from the committed inventories. Neither is edited by hand.